Debut 1990-1994

Calaway made his WWF debut as "Cain The Undertaker" at a taping of WWF Superstars on November 19, 1990.[9] The appearance of The Undertaker's first Deadman persona was modeled after a mortician from old Western movies, wearing a trench coat and black hat with grey gloves and boot covers. Under this Deadman persona, he was "impervious to pain," something accomplished by Calaway no-selling his opponents' attacks. Calaway made his official on-camera debut on November 22 at Survivor Series as a heel when he was the mystery partner of Ted DiBiase's Million Dollar team, where he was simply called The Undertaker.[10] Approximately one minute into the match, Undertaker eliminated Koko B. Ware with his finisher, the Tombstone Piledriver. He also eliminated Dusty Rhodes before being counted out. Shortly after Survivor Series, "Cain" was dropped from his name, and he was called simply The Undertaker. It was at this time that The Undertaker switched managers from Brother Love to Paul Bearer — a histrionic, ghostly character, almost always seen bearing an urn from which The Undertaker drew mystical power from, reviving his strength during his matches. After defeating his opponents in the ring, he would perform a post-match ritual which involved him putting his defeated opponent in a bodybag and carrying him to the back.[11]
He made his WrestleMania debut at WrestleMania VII, quickly defeating "Superfly" Jimmy Snuka.[12] The win was the first in his undefeated streak at the event. He began his first major feud with The Ultimate Warrior, when he attacked the Warrior and locked him in an airtight casket on the set of his manager, Paul Bearer's Funeral Parlour interview segment. After a year of battles with the Warrior, Randy Savage,[10] Sgt. Slaughter, and Hulk Hogan, he defeated Hogan to win his first WWF Championship at Survivor Series.[13] WWF President Jack Tunney ordered a rematch for This Tuesday in Texas six days later, where Undertaker lost the title to Hogan.[13]
In February 1992, Undertaker's ally Jake "The Snake" Roberts tried to attack Randy Savage's manager/wife Miss Elizabeth with a steel chair when Undertaker stopped him, becoming a fan favorite for the first time. Then, Undertaker defeated Roberts at WrestleMania VIII.[12] He then feuded extensively with wrestlers managed by Harvey Wippleman throughout 1992 and 1993, including Kamala,[13][14] whom he faced and defeated in the first televised coffin match in WWF history at Survivor Series, and Giant Gonzales, whom he defeated by disqualification at WrestleMania IX and by pinfall at SummerSlam in a "Rest in Peace" match.[12][14] In January 1994, he challenged WWF Champion Yokozuna to a casket match at the Royal Rumble. At the Royal Rumble, Yokozuna sealed Undertaker in the casket with the assistance of several other villainous wrestlers, winning the match. The Undertaker's "spirit" appeared from inside the casket on the video screen, warning that he would return.[15] This began Undertaker's first hiatus.